CA1309805C - Derive dipeptidique, sa synthese et son utilisation - Google Patents
Derive dipeptidique, sa synthese et son utilisationInfo
- Publication number
- CA1309805C CA1309805C CA000506770A CA506770A CA1309805C CA 1309805 C CA1309805 C CA 1309805C CA 000506770 A CA000506770 A CA 000506770A CA 506770 A CA506770 A CA 506770A CA 1309805 C CA1309805 C CA 1309805C
- Authority
- CA
- Canada
- Prior art keywords
- integer
- group
- carbon
- phenyl
- hydrogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 108010016626 Dipeptides Proteins 0.000 title claims abstract description 19
- 238000003786 synthesis reaction Methods 0.000 title abstract description 6
- 230000015572 biosynthetic process Effects 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims description 66
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 230000003496 anti-amnesic effect Effects 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 239000002475 cognitive enhancer Substances 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
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- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 239000003937 drug carrier Substances 0.000 claims 4
- 229940122210 Prolyl endopeptidase inhibitor Drugs 0.000 claims 2
- ORZXYSPOAVJYRU-UHFFFAOYSA-N benzyl 2-(2-formylpyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate Chemical compound O=CC1CCCN1C(=O)C1N(C(=O)OCC=2C=CC=CC=2)CCC1 ORZXYSPOAVJYRU-UHFFFAOYSA-N 0.000 claims 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
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- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
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- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 3
- VQDQISMDUHBUFF-UHFFFAOYSA-N 4-phenylbutanoyl chloride Chemical compound ClC(=O)CCCC1=CC=CC=C1 VQDQISMDUHBUFF-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06052—Val-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP80871/1985 | 1985-04-16 | ||
| JP60080871A JPH0623191B2 (ja) | 1985-04-16 | 1985-04-16 | ペプチダ−ゼ阻害活性化合物およびその製法ならびに用途 |
| JP60290237A JPH0651677B2 (ja) | 1985-12-23 | 1985-12-23 | ジペプチド誘導体及びその製法並びに用途 |
| JP290237/1985 | 1985-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1309805C true CA1309805C (fr) | 1992-11-03 |
Family
ID=26421833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000506770A Expired - Lifetime CA1309805C (fr) | 1985-04-16 | 1986-04-16 | Derive dipeptidique, sa synthese et son utilisation |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4873342A (fr) |
| EP (1) | EP0201741B1 (fr) |
| CA (1) | CA1309805C (fr) |
| DE (1) | DE3680578D1 (fr) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4880827A (en) * | 1986-03-18 | 1989-11-14 | Sumitomo Pharmaceuticals Company, Ltd. | Pyrrolidine derivatives having inhibitory action for proline specific endopepidase |
| US5254550A (en) * | 1986-11-20 | 1993-10-19 | Ono Pharmaceutical Co., Ltd. | Prolinal derivatives and pharmaceutical compositions thereof |
| EP0268190B1 (fr) * | 1986-11-20 | 1993-06-16 | Ono Pharmaceutical Co., Ltd. | Dérivés du prolinal |
| EP0277588B1 (fr) * | 1987-02-04 | 1993-03-24 | Ono Pharmaceutical Co., Ltd. | Dérivés du prolinal |
| DE3855875T2 (de) * | 1987-02-23 | 1997-08-28 | Ono Pharmaceutical Co | Thiazolidin-Derivate |
| DE3712365A1 (de) * | 1987-04-11 | 1988-10-27 | Hoechst Ag | Neue 2-acylpyrrolidin-derivate, verfahren zu ihrer herstellung, sie enthaltende mittel sowie deren verwendung |
| DE3712364A1 (de) * | 1987-04-11 | 1988-10-27 | Hoechst Ag | Neue pyrrolidin-2-(1,3-dicarbonyl)-derivate, verfahren zu ihrer herstellung, sie enthaltende mittel sowie deren verwendung |
| JP2691442B2 (ja) * | 1989-02-20 | 1997-12-17 | 株式会社ヤクルト本社 | 新規なプロリン誘導体 |
| EP0419683A4 (en) * | 1989-04-13 | 1992-03-11 | Japan Tobacco Inc. | New amino acid derivatives having prolylendopeptidase inhibitor activity |
| DK0536399T3 (da) * | 1990-06-07 | 1996-06-03 | Zeria Pharm Co Ltd | Hidtil ukendt arylalkanonylaminderivat og lægemiddel indeholdende samme |
| JP3810097B2 (ja) * | 1993-01-15 | 2006-08-16 | 明治製菓株式会社 | ピロリジン−２−イルカルボニル複素環式化合物誘導体 |
| EP0770091B1 (fr) * | 1994-05-12 | 2000-03-01 | Balazs Sarkadi | Composes servant a annihiler la resistance a des agents therapeutiques medicamenteux |
| IL128118A0 (en) * | 1996-09-10 | 1999-11-30 | Thomae Gmbh Dr K | Modified amino acids medicaments containing these compounds and processes for their preparation |
| US6313097B1 (en) | 1999-03-02 | 2001-11-06 | Boehringer Ingelheim Pharma Kg | Antagonists of calcitonin gene-related peptide |
| US6121311A (en) * | 1999-04-28 | 2000-09-19 | Japan Tobacco Inc. | Method for treating cocainism |
| FI20030014A0 (fi) * | 2003-01-03 | 2003-01-03 | Orion Corp | Prolyylioligopeptidaasia inhiboivaa aktiivisuutta omaavia yhdisteitä |
| JP4806628B2 (ja) | 2003-05-05 | 2011-11-02 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤 |
| US20050137142A1 (en) | 2003-11-03 | 2005-06-23 | Probiodrug Ag | Combinations useful for the treatment of neuronal disorders |
| WO2006058720A2 (fr) * | 2003-11-03 | 2006-06-08 | Probiodrug Ag | Nouveaux composes pour le traitement de troubles neurologiques |
| US7667044B2 (en) | 2003-11-03 | 2010-02-23 | Probiodrug Ag | Compounds for the treatment of neurological disorders |
| AU2005210004B2 (en) | 2004-02-05 | 2010-10-28 | Probiodrug Ag | Novel inhibitors of glutaminyl cyclase |
| ATE492532T1 (de) * | 2004-03-26 | 2011-01-15 | Dsm Ip Assets Bv | Aminosäure- und peptid-konjugate von arylalkylsäuren zur verwendung in der kosmetik |
| EP1760076A1 (fr) * | 2005-09-02 | 2007-03-07 | Ferring B.V. | Inhibiteur de FAP |
| EP2089383B1 (fr) | 2006-11-09 | 2015-09-16 | Probiodrug AG | Dérivés 3-hydr0xy-1,5-dihydr0-pyrr0l-2-one utiles en tant qu' inhibiteurs de la glutaminyl-cyclase dans le traitement des ulcères, du cancer et d'autres maladies |
| US9126987B2 (en) | 2006-11-30 | 2015-09-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| US8015671B2 (en) * | 2007-02-28 | 2011-09-13 | Illinois Tool Works Inc. | Strap with enhanced stiffness |
| AU2008220785B2 (en) | 2007-03-01 | 2013-02-21 | Vivoryon Therapeutics N.V. | New use of glutaminyl cyclase inhibitors |
| US9656991B2 (en) | 2007-04-18 | 2017-05-23 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| PL2475428T3 (pl) | 2009-09-11 | 2015-12-31 | Probiodrug Ag | Pochodne heterocykliczne jako inhibitory cyklazy glutaminowej |
| US9181233B2 (en) | 2010-03-03 | 2015-11-10 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| DK2545047T3 (da) | 2010-03-10 | 2014-07-28 | Probiodrug Ag | Heterocycliske inhibitorer af glutaminylcyclase (QC, EC 2.3.2.5) |
| WO2011131748A2 (fr) | 2010-04-21 | 2011-10-27 | Probiodrug Ag | Nouveaux inhibiteurs |
| EP2686313B1 (fr) | 2011-03-16 | 2016-02-03 | Probiodrug AG | Dérivés de benzimidazole en tant qu'inhibiteurs de la glutaminyl cyclase |
| PL3461819T3 (pl) | 2017-09-29 | 2020-11-30 | Probiodrug Ag | Inhibitory cyklazy glutaminylowej |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL58849A (en) * | 1978-12-11 | 1983-03-31 | Merck & Co Inc | Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them |
| JPS60172929A (ja) * | 1984-02-17 | 1985-09-06 | Yakult Honsha Co Ltd | 抗健忘症剤 |
| JPS60188317A (ja) * | 1984-03-09 | 1985-09-25 | Yakult Honsha Co Ltd | 抗健忘症剤 |
| JPS6137764A (ja) * | 1984-07-31 | 1986-02-22 | Suntory Ltd | 抗プロリルエンドペプチダ−ゼ活性を有する新規生理活性化合物 |
-
1986
- 1986-04-16 CA CA000506770A patent/CA1309805C/fr not_active Expired - Lifetime
- 1986-04-16 DE DE8686105231T patent/DE3680578D1/de not_active Expired - Lifetime
- 1986-04-16 EP EP86105231A patent/EP0201741B1/fr not_active Expired
- 1986-04-16 US US06/852,710 patent/US4873342A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0201741A3 (en) | 1989-02-08 |
| US4873342A (en) | 1989-10-10 |
| DE3680578D1 (de) | 1991-09-05 |
| EP0201741A2 (fr) | 1986-11-20 |
| EP0201741B1 (fr) | 1991-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |